Was That Timothée Chalamet at the Prada Show?

This is an edition of the newsletter Show Notes, in which Samuel Hine reports from the front row of the fashion world. Sign up here to get it free.

In recent seasons, the well-oiled fashion machine known as Prada has gone completely haywire. Miuccia Prada, the Milan fashion house’s cerebral co-creative director, is known for defining philosophical but specific themes in her work. Mrs. Prada (as she’s called) might go in on corduroy and cowrie shells one season, then reverse course and propose futuristic jumpsuits the next, indulging her well-regarded appetite for contradiction through clear creative statements.

Not anymore. Mrs. Prada and her creative partner Raf Simons don’t use moodboards to explain their work (please!), but if they did, you might suspect to find someone like the reigning prince of menswear chaos Timothée Chalamet creeping behind the Prada Fall-Winter 2025 men’s collection.

Guests entering the Fondazione Prada on the Sunday afternoon of Milan Fashion Week navigated a warren-like tower of scaffolding, the latest of Prada collaborator Rem Koolhaas’s wow-inducing set designs. Celebrities and press sat on the third floor, buyers and other grandees filed in below. There was nightclub lighting above and an art nouveau-style carpet (courtesy of Moulin Rouge! and The Great Gatsby set designer Catherine Martin) below, and the room was filled with a cyber beat punctuated by an underwater-dub chant: Technology! Technology! Mused Simons backstage, “It’s supposed to make you think about several references. Harsh contrasts…You could think: Is this Blade Runner, or is this some kind of ballroom in the twenties?”

The clothes stimulated the same juxtapositions, as if a sturdy scaffolding of references collapsed into a jumble of sartorial pickup sticks. Models wore colorful Western boots that terminated in stabby points; swathes of roughly-cut fur; plaid dressing gowns; clingy, citrusy Hawaiian-print undershirts; mechanic jackets; leather suits; skintight trousers; cocooning snorkel parka hoods cut off from their coats and worn as hats; pajama tops and bottoms; and, most dissonantly, tiny earrings and bracelets shaped like basketballs. It was as if Simons and Mrs. Prada had raided a Minnesota thrift store then dressed their cast in the dark.

The lineup also brought to mind Chalamet and the bizzaro assemblages of designer fashion, vintage garments, and kitschy merch he’s been wearing on his Gonzo press tour for A Complete Unknown. The actor is the most compelling style figure of our time because he reacts to his increasing fame not by smoothing his edges, but by getting increasingly weird. I once referred to his manner of dressing as post-swag, a whirlybird style that defies logic, resists trends, and ignores the often cumbersome history of menswear that so much contemporary fashion is still measured against. Now guided by stylist Taylor McNeill, Chalamet’s outfits have only gotten more wrong. But there’s a sense of impulsive freedom to them that also feels right. You can already picture Chalamet wearing one of the Prada basketball earrings—anywhere but a pickup basketball game, of course.

Some of the trousers and pajama pants were so tight they awkwardly clung to the models’ legs and boots, a Chalamet style signature if there was one. Backstage, with dozens of international critics and journalists hanging on her every word, Mrs. Prada explained that she and Simons were guided by emotion and intuition rather than cold hard reason: “It was about romance, inspiring passion, liberating instinct, which is so crucial at the moment. We spoke last season of artificial intelligence, and this is how to again go into humanity, passion, instinct—liberating that, basically.” Mrs. Prada was referencing a September show that featured a similarly bananas clash of seemingly irrational references, a response—as she said at the time—to the rise of algorithm-mediated taste. She is more interested in a lifestyle that follows personal proclivity wherever it goes.

Courtesy of Getty Images / Daniele Venturelli

Courtesy of Getty Images / Daniele Venturelli

The mashup also felt uncannily American. More than one person remarked to me after that the reminded them of Simons’s short tenure at Calvin Klein, where he turned his fascination with David Lynch and other domestic cinematic touchstones into spooky American tableaus. Were the cowboy-inflected clothes, unveiled on Trump inauguration eve—and, coincidentally, on the day where TikTok was unavailable to the many American influencers wearing Prada in the front row—also a nod to our new political paradigm, with tech overlords like Elon Musk headed for the White House? Mrs. Prada was circumspect: “It’s a bit of an answer as always to what is happening.”

With Prada, things are never quite so simple. Last year, I got the sense that the Prada braintrust was shifting their process away from theme-driven design and toward a more organic dialogue where they mix and blend and layer their points of inspiration to unpredictable ends, interpreting and reinterpreting their own work as they go. Backstage, Simons explained that the collection’s buzzwords, instinct and humanity, were more like keys to their evolving creative partnership: “It’s the process that is for us very interesting and important right now, to work very instinctively and kind of savage—savage in the sense that things can come together even if they seem like they’re not supposed to be together.”